Reaktion #59545

Reaktionsgleichung

HCl

potassium tert-butoxide

2-(2,5-Difluorophenyl)chroman-6-ol

1-chloro-4-ethoxy-2-nitrobenzene

→

2-(2,5-Difluorophenyl)-6-(4-ethoxy-2-nitrophenoxy)chroman

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 8 hours
2. 2
   workup.ADDITIONwas added into the reaction mixture and it
3. 3
   Extraktionwas extracted with ethyl acetate
4. 4
   WaschenThe combined organic extracts were washed with water and saturated NaCl-solution
5. 5
   SonstigeThe product was purified by column chromatography

Vorschrift

320 mg of 2-(2,5-Difluorophenyl)chroman-6-ol (Example 14(c)) was dissolved in dry DMF and potassium tert-butoxide (150 mg) was added. The resulting mixture was stirred for 30 minutes and 1-chloro-4-ethoxy-2-nitrobenzene (250 mg) was added. The reaction mixture was refluxed for 8 hours. After cooling to room temperature 1 M HCl-solution was added into the reaction mixture and it was extracted with ethyl acetate. The combined organic extracts were washed with water and saturated NaCl-solution. The product was purified by column chromatography using heptane-ethyl acetate (3:1) as an eluant. 1H NMR (300 MHz, CDCl3) δ: 7.43 (d, 1H, J 2.9Hz), 7.25 (m, 1H), 7.08-6.97 (m, 4H), 6.89-6.75 (m, 3H), 5.31 (d, 1H, J 9.1 Hz), 4.06 (q, 2H, J 7.0 Hz), 2.97 (m, 1H), 2.74 (m, 1H), 2.26 (m, 1H), 1.98 (m, 1H), 1.44 (t, 3H, 7.0 Hz).

Quelle